Startup mentors discuss strategies and challenges of creating a new business.

Ed Zimmerman: A 9/11 Victim’s Timeless Wisdom

ED ZIMMERMAN: I spent almost all of 1998 working on a single deal. It had many moving parts, and was really several deals, each of which hinged upon the others. Our client had a wonderful inside general counsel named Clarin Schwartz. Clarin was a seasoned lawyer who specialized in ERISA, a complex and esoteric area of law that deals with pensions and employee benefits. Despite her specialty, she found herself running a deal that was mostly M&A, equity and debt financing and intellectual property — and she handled it with grace, finesse and confidence.

I got to know Clarin very well over the course of that year. She was an incredible person who decided that she’d be a mentor to me rather than just a client. We had a terrific working relationship and she had a profound impact on the way I work with clients today. She gave me advice that I have subsequently found myself regularly imparting to others — junior lawyers, clients, my students at Columbia Business School and even my kids.

Clarin and I remained in steady contact after the deal closed, but she was killed in the September 11 terrorist attack on the World Trade Center. I think of her often and have been meaning to pass along some of her guidance. Here is my best attempt.

1. Bad news isn’t wine; it doesn’t get better with age.

I can’t recall the details of the bad news I had to communicate to Clarin, but I have a vivid recollection of how she reacted. In essence, she thanked me for having raised the problem so quickly, and appreciated that it wasn’t a phone call I’d been looking forward to making. She was right. When someone disarms you by handling bad news in that way, it makes it very easy to be transparent with him or her.

This sharply contrasts with what one of my friends who worked as a trader told me when describing how his office functioned. His firm operated on what he called “the chain of hate.” Each person in the corporate chain of command was more volatile than the next.

Traders, in particular, often find themselves in need of delivering bad news because not every trade is a good one. As a result of the chain of hate, being transparent and sharing bad news rapidly was very difficult for his team. While the advice I now regularly dispense is “bad news doesn’t get better with age,” it really translates into the following advice for managers, clients and senior executives: Create a culture in which it is easy to rapidly and transparently share bad news; it will make the organization stronger and foster trust. There’s a yin and yang to every relationship – the burden of honesty does not rest on only one party.

2. Mess up the hard stuff, not the easy stuff.

My recollection is that the bad news I had to deliver to Clarin that time wasn’t something of my own doing, but I sure do know that a later mess-up was. I had submitted a memo — it hardly matters whether I’d failed to review the work of the junior lawyer I was supervising, or whether the typos were my own — but I do know that the memo in question contained typos.

Clarin, I believe, subscribed to the up/down approach to feedback. She complimented the substance of the memo, but also said to me something like: “The substance was great; that was really hard stuff — but typos?” She then said something I have subsequently found myself repeating often: “Mess up the hard stuff, because if you get the easy stuff wrong, people who don’t know any better about the hard stuff will mistrust it.”

I think I was somewhat careful about typos prior to that conversation, but I know that I doubled down in the 15 years since. She was spot on: A client who doesn’t have independent knowledge of the substance of what we’re explaining is likely to be suspicious of our analysis if we deliver it with poor grammar or typos. By the way, this advice doesn’t apply solely to written work!

This next piece of advice is something she demonstrated rather than told me:

3. “Crazy” works.

Our deal involved multiple simultaneous closings occurring in real time in separate conference rooms in our office. (Back in 1998, lawyers didn’t close deals like this through email). In one closing, the lawyer for one of the parties (whose millions of dollars we really needed, or none of the deals would happen), issued a brand new and very onerous request that would have derailed everything. I pressured him, noting that it would have been customary to have made this request weeks, or even months, earlier. He conceded that I was correct, but that it hardly mattered as to whether that was his fault: His client had the money and my client wanted that money.

I shared this development with Clarin immediately (knowing that bad news doesn’t get better with age). At Clarin’s request, we gathered all the senior business people and lawyers into one room and Clarin asked me to repeat my message there. As I explained the issue and the timing of the request, Clarin, her back to the rest of us, poured herself a cup of coffee. Clarin was a buttoned-up lawyer in her late 40s at the time, normally supernaturally calm, but she came completely unwound as I spoke. She spun around quickly and began gesticulating wildly with the hand that held that hot coffee. She raised her voice, which I hadn’t heard her do before. She wasn’t yelling at anyone in particular, she was just sort of losing it. Coffee began speckling the floor, the table (which had original closing documents all over it) and the anxiety and discomfort of everyone in the room – especially me – became palpable. I put an arm around Clarin’s shoulder, fearful that our deal was going to bust and that my client had blown a gasket. I walked her outside, saying to the others, “I’m going to confer with my client in private for a minute.”

I was sweating. I asked Clarin if she was OK. She responded: “Do you think that worked?” The whole thing had been contrived. She knew that the lawyer was justified in making his request, and had likely missed the issue earlier and didn’t want his client to know this. Time was short and as I’ve already indicated, a problem on this deal could have had a domino effect on all the others. Clarin hadn’t wanted the coffee at all: Her performance had been designed to inform everyone in that room that she was going to go all kinds of crazy if this misstep on their part blew up the deal.

Clarin had us wait outside to ensure that people believed it was long enough for her to have calmed down. When we reentered, the lawyer promptly rescinded his ask and the deals were all back on as if nothing had happened. We closed everything that day.

I am not sure what I learned from that last one, but it was a masterful stroke, because sometimes there’s not enough time to conduct a rational negotiation. Maybe thinking outside the box and playing against type were the major takeaways from that lesson. I certainly learned about coffee stains that day!

4. What she didn’t say.

What Clarin didn’t say was that some people approach the attorney/client relationship the way you approach a vending machine: Put the money in and out comes the candy. Very simple. Others see it as an opportunity to build better bonds and even to mentor their lawyers. Clarin created a context in which it was very easy to tell her anything. And because she was so good to me and to our firm, I worked as hard as I could for her, and told her how much I appreciated her approach.

Ed Zimmerman

Ed Zimmerman with rocker Lou Reed in an undated photo.

My father passed away in 1993. He loved opera and idolized Jan Peerce, a famous mid-century singer of both opera and Hebrew cantorial music. My dad once met Peerce and told him how much he appreciated his work. My father told me that it was important to “send flowers while they’re still around,” and he included famous people in this dictum.

I’ve been fortunate to have applied his advice numerous times, including during a dinner I once attended with Lou Reed, a rocker I’d idolized as a teenager and still listen to regularly. I told Reed how much his “Magic and Loss” album had meant to me when I was making daily visits to the hospital as my father was dying. Reed was incredibly gracious and clasped both his hands around mine and thanked me — just an incredible experience.

My dad also felt the advice applied to thanking those around you every day. It makes me very sad that I can no longer “send flowers” to Clarin, but I hope that recalling some of her kindness, generosity, advice and good humor will help others form strong and lasting relationships in their own dealings. Just keep some stain remover on hand!

Comments (5 of 10)

I'm guessing you've actually mentored way more than 2 people JHE. Thanks for the thoughtful comments and I am sorry to hear that 9/11 is an especially terrible day for you, as it is for so many. I find it to be a very sad and reflective day but also one that does underscore how lucky many of us got that day

11:59 am September 12, 2013

JHE wrote:

9/11 is often a terrible day for many people. It certainly often is for me. Using it as an opportunity to reflect on those that we lost and the lessons that we learned from them is inspiring.

I was luck enough to have a boss early in my career who mentored me. And I needed a lot of it. Mentoring is one of those things that can't be artificially constructed but must evolve organically. Despite handing out advice ad nauseum, think I've mentored only two people in my career. Both times I got as much from it as they did

6:25 pm September 11, 2013

Jason D wrote:

Good stuff Ed. Thanks for passing it on....

12:21 pm September 11, 2013

Rekha P wrote:

thank you for this post Ed.

All valuable life lesions….and indeed the one about how one handles bad news and disarms the other person is very touching. Brings to mind the time I first told a patient all on my own that he had cancer which would take his life in six months.... the words would just not come out as I faced this man and his wife.
He very gently told me “ this is really hard for you isnt it?” and helped me to tell him the news. I have never forgotten that level of grace that he , this older man, receiving the worst news of his life, showed a young doctor who was trying……..

Anyway, each one of the points you write about brought home valuable life lessons and remembrances…something we should all do on this day….

thank you again, rekha

12:07 pm September 11, 2013

Jess B wrote:

Amazing post Ed, and so timely. Thank YOU for making me pause and reflect, and be grateful on this day.

About The Accelerators

For aspiring or actual entrepreneurs, The Accelerators is an online archive of discussion among startup mentors– entrepreneurs, angel investors and venture capitalists. Although the blog is no longer being updated, its content lives here and you can see an archive of its tweets through June 2015 @wsjstartup.